Near East Side Holidays

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  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$616 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Our guide on where to stay in Near East Side

Find the best Near East Side areas and neighborhoods for the activities you enjoy most. Learn more about Near East Side
Downtown Chicago featuring a city

Downtown Chicago

4 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Our pick of the best Near East Side Hotel Deals

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$295 per night from 22 Feb to 23 Feb
NZ$295
22 Feb - 23 Feb
includes taxes & fees
9/10 Wonderful! (3,181 reviews)
Great room. Beautiful view. Wonderful service from the staff.

Reviewed on 11 Feb 2026

Swissotel - Chicago
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
221 N Columbus Dr Chicago IL
The price is NZ$374 per night from 22 Feb to 23 Feb
NZ$374
22 Feb - 23 Feb
includes taxes & fees
8.4/10 Very Good! (1,854 reviews)
We had a really good stay here. Really nice staff, clean room, fairly quiet. Really nice! In a great spot to just walk around.

Reviewed on 12 Feb 2026

Radisson Blu Aqua Hotel Chicago
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$369 per night from 13 Mar to 14 Mar
NZ$369
13 Mar - 14 Mar
includes taxes & fees
8/10 Very Good! (9,882 reviews)
Great location, beautiful historic hotel with clean, updated rooms.

Reviewed on 11 Feb 2026

Congress Plaza Hotel
See all 4,663 properties in Near East Side
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Near East Side holiday package cost?
Say yes to new adventures with our Near East Side holiday packages, which start from a low . Select the hotels and flights that suit your style. Then, add on a couple of enriching experiences for an unforgettable getaway.
How do I get a cheap travel package to Near East Side?
By bundling. Hotels, rental cars and flights — combine whatever you need into a Near East Side holiday package and save. Score even more bargains when you add extras such as sightseeing tours to your booking. But that's not the only impressive part. You have the freedom to put together your trip your way. We offer more than 550 airlines and 1 000 000 properties globally, so that everyone has a chance to travel and fulfil those holiday fantasies.
Where should I stay in Near East Side?
Most visitors to Near East Side include both McCormick Place and Millennium Park on their bucket lists. Why not select a hotel within walking distance of these popular attractions?
What are the top hotels in Near East Side?
Book a stay at Swissotel - Chicago. It's one of this area's most popular hotels. Another top-rated option in Near East Side is Radisson Blu Aqua Hotel Chicago.
How far in advance should I book my Near East Side holiday?
It's always wise to book early. Airlines generally release flights up to a year ahead of departure, and this is a great opportunity to land some of the cheapest prices. Boss just told you to use up your holiday time next month? That's alright! Expedia are never short of fantastic bargains to send you off on the getaway of your dreams, at a price you can afford.
What does an Expedia Near East Side travel package include?
Car rentals, hotels and flights — we bring you all the best deals. All you'll have to do is select your preferred combination. After you've made your booking, you can add on the fun stuff like tours and experiences. Our travel packages make it easy to customize an exciting Near East Side getaway.
What should I know before booking a Near East Side travel package?
You'll enjoy excellent savings when you bundle your hotels, flights and rental cars into a package. Plus, booking everything in one spot makes trip planning much easier. So why waste your money or time? Whether you're organising a ritzy city getaway or a budget family adventure, take a look at our holiday packages today.
Can I choose my airline with a Near East Side Expedia holiday package?
Expedia offers access to more than 550 airline partners worldwide, so you sure can! Just pick the carrier you want and craft the perfect Near East Side escape.
If I'm not able to travel, can I cancel my Near East Side holiday package?
Whether it's your hotel, flight or rental car, you can cancel and rebook it. Locked in your Near East Side holiday package in the last 24 hours? You may be able to make changes at no cost. If it's been longer than that, you may incur a fee from your airline, hotel or car rental company. For more information, visit our Customer Service Portal. We're here to help you every step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.